CN1036653C - 含哌啶环的螺杂环化合物的制备方法 - Google Patents
含哌啶环的螺杂环化合物的制备方法 Download PDFInfo
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- CN1036653C CN1036653C CN88109138A CN88109138A CN1036653C CN 1036653 C CN1036653 C CN 1036653C CN 88109138 A CN88109138 A CN 88109138A CN 88109138 A CN88109138 A CN 88109138A CN 1036653 C CN1036653 C CN 1036653C
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229910001562 pearlite Inorganic materials 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP252104/87 | 1987-10-05 | ||
| JP25210487 | 1987-10-05 | ||
| JP286297/87 | 1987-11-12 | ||
| JP28629787 | 1987-11-12 | ||
| JP84327/88 | 1988-04-05 | ||
| JP8432788 | 1988-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1033629A CN1033629A (zh) | 1989-07-05 |
| CN1036653C true CN1036653C (zh) | 1997-12-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88109138A Expired - Fee Related CN1036653C (zh) | 1987-10-05 | 1988-10-05 | 含哌啶环的螺杂环化合物的制备方法 |
Country Status (14)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0311313B1 (en) * | 1987-10-05 | 1995-05-10 | Yamanouchi Pharmaceutical Co. Ltd. | Heterocyclic spiro compounds and their preparation |
| US5412096A (en) * | 1987-10-05 | 1995-05-02 | Yamanouchi Pharmaceutical Co., Ltd. | Hydrochloride salts of heterocyclic spiro compounds |
| US5594000A (en) * | 1989-06-21 | 1997-01-14 | Astra Ab | Spirofurane derivatives |
| US5075317A (en) * | 1989-06-21 | 1991-12-24 | Fisons Corporation | Spirofurane derivatives |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| US5407938A (en) * | 1990-04-10 | 1995-04-18 | Israel Institute For Biological Research | Certain 1-methyl-piperidine-4-spiro-4'-(1'-3'-oxazolines) and corresponding -(1',3' thiazolines) |
| US5852029A (en) * | 1990-04-10 | 1998-12-22 | Israel Institute For Biological Research | Aza spiro compounds acting on the cholinergic system with muscarinic agonist activity |
| US5073560A (en) * | 1990-07-20 | 1991-12-17 | Fisons Corporation | Spiro-isoxazolidine derivatives as cholinergic agents |
| IE914238A1 (en) * | 1990-12-19 | 1992-07-01 | Fisons Corp | Novel spirofurane derivatives |
| WO1992020683A1 (en) * | 1991-05-15 | 1992-11-26 | Yamanouchi Pharmaceutical Co., Ltd. | (-)-(s)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4,5]decane l-tartrate |
| EP0681571B1 (en) * | 1993-01-28 | 1998-07-29 | Merck & Co. Inc. | Spiro-substituted azacycles as tachykinin receptor antagonists |
| WO1994020500A1 (en) * | 1993-03-04 | 1994-09-15 | Pfizer Inc. | Spiroazacyclic derivatives as substance p antagonists |
| JP2983141B2 (ja) * | 1993-10-06 | 1999-11-29 | 株式会社三和化学研究所 | 新規化合物及び該化合物を有効成分とする脳機能改善剤 |
| AU744368B2 (en) | 1997-05-30 | 2002-02-21 | Neurosearch A/S | Spiro-quinuclidine derivatives, their preparation and use |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| SE9900100D0 (sv) * | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| WO2001011968A2 (en) * | 1999-08-13 | 2001-02-22 | Aventis Cropscience Gmbh | Heterocyclic spiro compounds as pesticides |
| AU2001253597A1 (en) * | 2000-04-12 | 2001-10-30 | Minerva Biotechnologies Corporation | Treatment of neurodegenerative disease |
| JP2003063964A (ja) * | 2001-08-28 | 2003-03-05 | Senju Pharmaceut Co Ltd | ドライアイまたはドライアイを伴なう疾病の予防治療剤 |
| JP5254616B2 (ja) | 2004-09-13 | 2013-08-07 | クロノ セラピューティクス、インコーポレイテッド | 生物学的同調性（ｂｉｏｓｙｎｃｈｒｏｎｏｕｓ）経皮的薬物送達 |
| CN101232882A (zh) * | 2005-07-26 | 2008-07-30 | 千寿制药株式会社 | 经皮吸收性眼用制剂 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| WO2007025177A2 (en) * | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2007104035A1 (en) * | 2006-03-08 | 2007-09-13 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US20100216734A1 (en) * | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| MX2008014320A (es) * | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| US20100009983A1 (en) * | 2006-05-09 | 2010-01-14 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| ITMI20061279A1 (it) * | 2006-06-30 | 2008-01-01 | Consiglio Nazionale Ricerche | Agonisti nicotinici selettivi per il sottotipo recettoriale alfa7,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US7998971B2 (en) | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CA2663347A1 (en) * | 2006-09-19 | 2008-03-27 | Braincells, Inc. | Ppar mediated modulation of neurogenesis |
| US20080103105A1 (en) * | 2006-09-22 | 2008-05-01 | Braincells, Inc. | HMG CoA REDUCTASE MEDIATED MODULATION OF NEUROGENESIS |
| AU2008232453B8 (en) | 2007-04-02 | 2011-07-21 | Parkinson's Institute | Methods and compositions for reduction of side effects of therapeutic treatments |
| EP2389383B1 (en) | 2009-01-26 | 2019-04-24 | Israel Institute For Biological Research | Bicyclic heterocyclic spiro compounds |
| US9034891B2 (en) | 2009-01-26 | 2015-05-19 | Israel Institute For Biological Research | Bicyclic heterocyclic spiro compounds |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| EP2882428B1 (en) | 2012-07-13 | 2019-01-16 | Pain Therapeutics, Inc. | A method of inhibiting tau phosphorylation |
| US9433604B2 (en) | 2013-10-08 | 2016-09-06 | Pain Therapeutics Inc. | Method for inhibiting growth of cancer cells |
| US10213586B2 (en) | 2015-01-28 | 2019-02-26 | Chrono Therapeutics Inc. | Drug delivery methods and systems |
| WO2018129304A1 (en) | 2017-01-06 | 2018-07-12 | Chrono Therapeutics Inc. | Transdermal drug delivery devices and methods |
| US11596779B2 (en) | 2018-05-29 | 2023-03-07 | Morningside Venture Investments Limited | Drug delivery methods and systems |
| CA3119992A1 (en) | 2018-11-16 | 2020-05-22 | Morningside Venture Investments Limited | Thermally regulated transdermal drug delivery system |
| CN115124545B (zh) * | 2022-08-31 | 2023-01-03 | 南京远淑医药科技有限公司 | 一种促性腺激素释放激素受体拮抗剂中间体的合成方法 |
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| US4321379A (en) * | 1981-01-28 | 1982-03-23 | American Cyanamid Company | 4-Aryl-1-oxa-8-azaspiro[4,5]dec-3-en-2-ones |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305556A (en) * | 1962-11-23 | 1967-02-21 | Pfizer & Co C | Novel hypoglycemic agents |
| NL124853C (enrdf_load_stackoverflow) * | 1963-07-19 | |||
| SU335944A1 (ru) * | 1970-12-15 | 1976-01-25 | Научно-исследовательский институт химии Саратовского государственного университета им.Н.Г.Чернышевского | Способ получени соединений р да 1-окса6-азаспиро(4,4)нонана |
| GB1301254A (enrdf_load_stackoverflow) * | 1971-07-08 | 1972-12-29 | ||
| US3784551A (en) * | 1971-07-08 | 1974-01-08 | Yoshitomi Pharmaceutical | 2-oxo-1,4-dioxa-8-azaspiro (4.5) decanes and related compounds |
| US3839273A (en) * | 1971-11-13 | 1974-10-01 | Sankyo Co | N-substituted piperidine derivatives, process for preparing the same and their use as stabilizers |
| SU434735A1 (ru) * | 1972-03-01 | 1975-12-15 | Научно-исследовательский институт химии Саратовского государственного университета им.Н.Г.Чернышевского | Способ получени 7-метил-(или 2,7диметил)-2-метокси- -пропионитрил1-окса-6-азаспиро-(4,4)-нонана |
| SU465399A1 (ru) * | 1973-07-19 | 1975-03-30 | Научно-исследовательский институт химии при Саратовском государственном университете им.Н.Г.Чернышевского | Способ получени натриевых солей 2-метокси- -карбоксиэтил-1-окса6-азаспиро-(4,4)-нонана |
| IL48452A (en) * | 1975-11-11 | 1979-07-25 | Purdue Frederick Co | Spiro (1,3-dioxolane-4,3') quinuclidines,their preparationand pharmaceutical compositions comprising them |
| SU1002294A1 (ru) * | 1981-08-14 | 1983-03-07 | Ордена Трудового Красного Знамени Институт Тонкой Органической Химии Им.А.Л.Мнджояна | 2,2-Диалкил-3-тиа-8-азаспиро/5,5/ундеканы |
| EP0189370A3 (de) * | 1985-01-16 | 1988-01-27 | Sandoz Ag | Spiro-dioxolane, -dithiolane und -oxothiolane |
| US4855290A (en) * | 1985-05-10 | 1989-08-08 | State Of Israel, Represented By Prime Minister's Office, Israel Institute For Biological Research | Derivatives of quinuclidine |
| US4981858A (en) * | 1987-08-13 | 1991-01-01 | State Of Israel, Represented By The Prime Minister's Office, Israel Institute For Biological Research | Optical isomers |
| EP0311313B1 (en) * | 1987-10-05 | 1995-05-10 | Yamanouchi Pharmaceutical Co. Ltd. | Heterocyclic spiro compounds and their preparation |
| US5073560A (en) * | 1990-07-20 | 1991-12-17 | Fisons Corporation | Spiro-isoxazolidine derivatives as cholinergic agents |
-
1988
- 1988-09-30 EP EP88309095A patent/EP0311313B1/en not_active Expired - Lifetime
- 1988-09-30 ES ES88309095T patent/ES2074441T3/es not_active Expired - Lifetime
- 1988-09-30 AT AT88309095T patent/ATE122353T1/de not_active IP Right Cessation
- 1988-09-30 DE DE3853758T patent/DE3853758T2/de not_active Expired - Lifetime
- 1988-10-03 CA CA000579193A patent/CA1337817C/en not_active Expired - Fee Related
- 1988-10-04 NO NO884406A patent/NO171109C/no unknown
- 1988-10-04 JP JP63251489A patent/JPH0236183A/ja active Granted
- 1988-10-04 DK DK554288A patent/DK554288A/da not_active Application Discontinuation
- 1988-10-05 CN CN88109138A patent/CN1036653C/zh not_active Expired - Fee Related
- 1988-10-05 KR KR1019880012963A patent/KR970007947B1/ko not_active Expired - Fee Related
- 1988-10-05 US US07/254,375 patent/US4940795A/en not_active Ceased
- 1988-10-05 AU AU23449/88A patent/AU621559B2/en not_active Ceased
-
1990
- 1990-01-25 US US07/470,093 patent/US5041549A/en not_active Expired - Fee Related
- 1990-01-25 US US07/470,091 patent/US4996210A/en not_active Expired - Fee Related
-
1992
- 1992-07-07 US US07/909,639 patent/USRE34653E/en not_active Expired - Lifetime
-
1995
- 1995-06-30 HU HU95P/P00638P patent/HU211687A9/hu unknown
- 1995-08-02 GR GR950402111T patent/GR3016995T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4321379A (en) * | 1981-01-28 | 1982-03-23 | American Cyanamid Company | 4-Aryl-1-oxa-8-azaspiro[4,5]dec-3-en-2-ones |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0311313A3 (en) | 1990-12-05 |
| ATE122353T1 (de) | 1995-05-15 |
| USRE34653E (en) | 1994-07-05 |
| GR3016995T3 (en) | 1995-11-30 |
| CN1033629A (zh) | 1989-07-05 |
| KR970007947B1 (ko) | 1997-05-19 |
| NO171109B (no) | 1992-10-19 |
| DK554288A (da) | 1989-05-26 |
| DE3853758D1 (de) | 1995-06-14 |
| JPH0236183A (ja) | 1990-02-06 |
| AU2344988A (en) | 1989-04-06 |
| US4996210A (en) | 1991-02-26 |
| KR890006649A (ko) | 1989-06-15 |
| CA1337817C (en) | 1995-12-26 |
| ES2074441T3 (es) | 1995-09-16 |
| NO884406D0 (no) | 1988-10-04 |
| US4940795A (en) | 1990-07-10 |
| DK554288D0 (da) | 1988-10-04 |
| EP0311313B1 (en) | 1995-05-10 |
| JPH0544948B2 (enrdf_load_stackoverflow) | 1993-07-07 |
| NO171109C (no) | 1993-01-27 |
| EP0311313A2 (en) | 1989-04-12 |
| AU621559B2 (en) | 1992-03-19 |
| HU211687A9 (en) | 1995-12-28 |
| US5041549A (en) | 1991-08-20 |
| DE3853758T2 (de) | 1995-09-07 |
| NO884406L (no) | 1989-04-06 |
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